There is an issue surrounding remap reloading when includes and plugin config files are used. These will not trigger a remap reload on their own. I think at this point everyone uses their external management tools to issue a touch to the remap file to trigger a reload to happen, but it's a bit of a work-around.
I'm proposing adding an API that will allow plugins to register their config files to be monitored in the same way that remap and records are currently monitored. When a traffic_ctl config reload is issued, if one of these files has changed that can also trigger a remap reload. I have a POC going currently where I can add an arbitrary file to trigger the reload but got to the point of looking at the API so figured I would send out a list message for any ideas/concerns/etc - Evan